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Potassium Carbonate → cis-7-Methoxy-4-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline

HRID 1421900
ノート
印刷プレビュー

反応式

HRID 1421900 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][O:16][C:17]1[C:30]2[CH2:29][CH2:28][C@H:27]3[C@H:22]([CH2:23][CH2:24][CH2:25][NH:26]3)[C:21]=2[CH:20]=[CH:19][CH:18]=1.[C:31]1([C:37]2[CH:50]=[CH:49][C:40]([C:41]([NH:43][CH2:44][CH2:45][CH2:46][CH:47]=O)=[O:42])=[CH:39][CH:38]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>ClC(Cl)C.C(OCC)(=O)C.CCCCC>[CH3:15][O:16][C:17]1[C:30]2[CH2:29][CH2:28][C@H:27]3[C@H:22]([CH2:23][CH2:24][CH2:25][N:26]3[CH2:47][CH2:46][CH2:45][CH2:44][NH:43][C:41](=[O:42])[C:40]3[CH:49]=[CH:50][C:37]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:38][CH:39]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 217125654-(4-Phenylbenzoylamino)butyraldehydeHCID 86654085cis-7-Methoxy-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline

生成物 1

HCID 86755478cis-7-Methoxy-4-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline収率 60%

試薬・触媒・溶媒

2
HCID 63651,1-Dichloroethane溶媒HCID 22335286Ethyl acetate pentane溶媒

実験手順

Sodium triacetoxyborohydride (1.5 g, 6.9 mmol) was added to a stirred mixture of cis-7-methoxy-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline (D6b, 1.0 g, 4.6 mmol) and 4-(4-phenylbenzoylamino)butyraldehyde (1.4 g, 5.1 mmol) in dichloroethane (50 ml) at room temperature. After stirring for 12 h, saturated aqueous K2CO3 (40 ml) was added and the mixture extracted into dichloromethane (3×20 ml). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a gum. Chromatography on silica, using 50-100% ethyl acetate/pentane as elution gradient, gave the title compound as a white solid (1.29 g, 60%).

後処理

  1. extractionthe mixture extracted into dichloromethane (3×20 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a gum
  6. washas elution gradient

出典と根拠

ORDレコード
ord-a95aab9ba6844463b0c4f4828b7d3176
出典データセット
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06080752

反応ノート

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